This Side of Paradise
by melancholicmermaid
Summary: Chuck Bass enters into a game to deflower the Virgin Queen, falls in love with his best friend's girl, and Blair Waldorf discovers an affinity for the dark side. AU
1. Chapter 1

**A.N -** AU where Chuck is 20 and Blair is 17.

* * *

 **Part 1**

The river bears no empty bottles, sandwich papers,

Silk handkerchiefs, cardboard boxes, cigarette ends

Or other testimony of summer nights. The nymphs are departed.

And their friends, the loitering heirs of city directors;

Departed, have left no addresses.

 **Chapter One**

The morning sun blazed over the Vanderbilt island drenching the new-mown grass and its various occupants in gilded light. The Vanderbilt family along with its many branches and a good number of their friends and associates were taking advantage of the balmy outdoors- the men engaged in a game of football, the women in the only slightly less competitive sport of sunning and gossip.

But right across this tableau of social merriment, a figure lay alone, reclining in the hammock that swung between a pair of pines. She had been reading A Lover's Discourse, firmly of the opinion that once she had mastered the deconstruction of love she would be cured of her own lovesickness, of her constant longing for a romantic grandeur that seemed only to exist in the world of Golden Age Hollywood. But this day even Barthes lovely prose couldn't satisfy her. Sighing, she dropped the book on her stomach and closed her eyes.

Blair Waldorf was bored, which was a rather dangerous condition, especially for those around her. It wasn't that she didn't enjoy the idle decadence of summer, and the private island right off the New England coast was certainly up to her standards, but the summertime indolence was causing her mind to drift off and wander, away from the present, and into the treacherous terrains of the past and future.

Suddenly, Blair had the strangest feeling of being stared at and opened her eyes to find a man walking right in her direction. Even now, as he reached her, his eyes travelled across her body, lingering at her chest and her bare legs in a way that made her decidedly uncomfortable.

"Little Blair Waldorf, not so little anymore," he sang, complete with a creepy grin.

Blair, annoyed that he knew her name when she seemed to fail to recognize him, asked in her bitchiest voice, "And who are you?"

"Call me uncle," he said, offering no other identification. But it was enough to trigger her memory and just as she was about to respond, the nephew himself materialized next to them.

Chuck Bass leaned against the tree and lit up a Gitanes as he looked between Blair and his uncle.

"I see you two have met."

"You didn't tell me Blair grew up too be so beautiful, Chuck," Jack said in a false chiding voice, "and you mention a lot of girls."

Chuck ignored this statement specifically because of its veracity. He had always found Blair distractingly pretty- but given that she was practically betrothed to his best friend, he found it in his best interests not to dwell on those thoughts.

Though there were times he slipped, he noted, looking at her stretched out on the hammock. Sometimes he was so keenly aware of her girlhood, her fragile softness, the rare display of skin, a lock of dark hair flowing in the summer wind and brushing her naked shoulder…

Distracting, yes, Chuck thought, tearing his gaze away, but not someone he had any intention of including in the conversations he had with his uncle.

"Jack is signing a deal with the Captain," he said instead, explaining his uncle's presence.

"When I last saw you, you were just a small thing, chasing after the Archibald boy," Jack continued, not taking his eyes off Blair.

"She's still pretty small and she's still chasing after Nathaniel, so I'd say not a lot has changed."

The book Blair was reading came flying at his head in response.

"Ow," he said rubbing his temple where the edge had hit him, "that could have seriously injured me."

"Quit being dramatic," she snapped, as she gracefully slid off of the hammock and stalked away from them.

After a split-second of deliberation, Chuck followed her.

"You know, I was expecting a better welcome."

"What's the point? I am sure you'll be gone in a day or two."

"No such luck, Waldorf. I am back in your life for good."

Blair paused and cautiously turned to look at Chuck. He didn't appear to be lying but then again, he was an accomplished liar. She would know. "After Tripp's wedding, you are moving back to the city?"

"Bart wants me to join him at Bass Industries."

"Chuck, that's wonderful!" she exclaimed, her anger forgotten as she regarded him. She remembered how much Chuck had once longed for this responsibility. Yet now, he seemed less than exuberant while delivering the news.

"I wouldn't count on it. Knowing my father, he has some trick up his sleeve. And not something that bodes well for me."

"Dartmouth kicked you out?" she hazarded a guess.

"You know me well," he said, with a bitter laugh.

"And if Bart wasn't able to to pay your way out of that mess it must have been a pretty serious offence."

"Even by my standards."

"So?"

"So what?"

"What did you do?!"

"Ah, that I am afraid is too scandalous for your ears. I wouldn't want to taint your innocence."

"I'll say it's a little too late for that, isn't it?"

Chuck looked at her, surprised, "Does that mean Nathaniel finally managed to-"

"Ugh, no. After his little indiscretion with S, I am torturing him a little longer. Anyway, I simply meant that I have already been privy to plenty of your exploits. It can't be any worse, can it?"

"Oh, you have no idea."

Blair wanted to press him further, her interest piqued, but was interrupted by the appearance of her boyfriend.

Nate Archibald bounded up to them, the epitome of athleticism and good breeding. Chuck, who always seemed best suited to exist in the dark shadows, should have hated this Golden Boy, who had since childhood lived a life which was the antithesis of Chuck's own. Contrary to all reason, however, this was his most lasting and successful relationship - the one person who had always trusted and accepted Chuck even while all of UES seemed to want his father's money but none respected it. Nouveau Riche, they used to whisper. And that was before Chuck grew up and made a mockery of his own reputation. Nate had never wavered from their friendship even when college had separated them.

Nate greeted him with a one-armed hug before slipping his hands around Blair's waist, pulling her close.

"Jack told me you're back. I can't believe you didn't call, man!"

"I thought I'd let it be a surprise," he drawled.

"Well, it certainly is a surprise. Sorry about Dartmouth, but it's good to have you back. And all of us, together again."

"Yeah, it certainly feels like old times," Chuck said, averting his eyes from them and looking at the sea in the distance. He had followed Blair blindly and she seemed to have led him straight to the private cove they used to access in summers past. A driftwood was lying innocently at his feet and he kicked it viciously, watching it crumble a little as it rolled away.

"Oh, speaking of old times, I know you just got here, but wanna play one of our classic games? I already have a target in mind. She's the worst, but she's also blonde and slutty so totally up your alley."

"If so, what am I doing in here and not in her? Lead the way," he smirked.

"Hey, Rachel is actually really nice. And you can't blame her for being a bridesmaid. Maureen picked her." Nate said, trying to be the voice of reason.

"I can and I will. She won't stop rubbing it in. Yesterday, she actually asked for my opinion on her dress pattern! As if!"

"How dare she," Chuck said, laughing.

"Don't encourage her, Chuck!" Nate said, shaking his head. He was glad to have his best friend back, but he always seemed to bring out the worst in Blair.

"Oh look, she's there," Blair pointed towards the girl, ignoring Nate.

"How do we even know this is gonna work," Nate said, making a weak last attempt to change their minds. "She has a boyfriend."

"Come on," Chuck said, walking backwards and pointing at himself, "it's gonna work."

And sure enough, they watched Chuck walk back into the house with her.

"Look, she's cheating on her boyfriend. Not really a nice person, is she?" Blair said innocently, looking up at Nate with her wide brown eyes.

"I guess not," Nate accepted, having discovered it was best to always agree with her. "Though sometimes good people make mistakes," he continued, taking her hand in his and looking penitent.

Blair, who had no wish to revisit her boyfriends past transgression just so he could assuage his guilt, snatched her hand away. Everytime Blair thought of his betrayal she felt unloved and ugly. All she wanted to do was never think of it again. So she erased the dark thoughts from her mind and smiled benevolently at him hoping it would shut him up about it.

It worked.

"Do you remember this tree?" he asked, looking up at the Willow they were standing under.

"It's where we had our first kiss," Blair said softly.

"I am glad we skipped the Hamptons this year." He leaned down and kissed her, his thumb grazing her cheek.

If Blair hadn't been distracted by the thought of her plan falling into place, she would have appreciated this moment with her boyfriend, sunlit and picturesque. But as it stood, she was rather distracted, and she quickly tore herself away.

"Okay, I am off to steer Rachel's boyfriend towards her room," Blair said, straightening her headband. "It's for his own good! He deserves to know the truth," she added hastily, incase Nate would decide to stop her.

* * *

"I would love to be your bridesmaid," Blair said graciously. "But it's too bad Rachel headed home early. I'll, uh, miss her."

Maureen smiled at her, "Thanks for stepping in, Blair."

"Yes, how kind of you, Blair," Chuck said, appearing just as Maureen turned to leave.

Blair beamed at him, happy that her latest ploy had worked, and also more than a little tipsy thanks to the free-flowing cocktails at the dinner party. Even she hadn't anticipated how soon she would be called upon to replace Rachel.

"Surprised you didn't go for the maid of honor position."

"Well, I would have to wrangle that away from Maureen's sister herself," she replied comfortably. For the first time since he had arrived, Blair found herself appraising Chuck. She had seen him on occasion in the past two years but looking at him now she felt the change was impressive. His cheekbones were...admirable and he had this new hairstyle which was rather easy on the eye. And his suit was impeccable. Blair just had the craziest urge to touch it. He had also grown taller.

"You've grown taller," she said, choosing to keep the rest of her observations to herself.

"That tends to happen." Chuck looked amused as he regarded her, and Blair wondered if he could read her mind. Embarrassed even of admitting to herself that she now found him attractive, Blair blushed. He was still Chuck, the sleazy manwhore, she reminded herself. Had he not managed to get laid less than an hour after getting off the ferry? (Never mind that Blair had orchestrated that herself.)

"I missed this," Chuck said, leaning closer to her ear.

"What?"

"This shade of your skin. Makes me wonder how far down the blush travels," he whispered, eyeing her cleavage.

"Ew," Blair groaned, pushing him away, "you are still as disgusting as ever."

"And you are still just as fun to rile up." And with that comment, Chuck walked away to join Nate at the bar.

Blair rolled her eyes at his words and grabbed a flute from a passing waiter. This was going to be a long summer.

* * *

A.N- Please review so I know you are reading this!?


	2. Chapter 2

**A/N-** Thanks so much for reviewing the first chapter! Uploading on ff net is so tedious, I was debating on just putting this up on Ao3 or tumblr, but the reviews make it worth my struggle!

* * *

 **Chapter 2**

Blair woke up with a start. She glanced at the bedside clock and saw that it was three in the morning. She had had the most vivid dream, though she seemed to have forgotten most of it already.

It had started out as a memory, from the summer when she was twelve. She and Serena had snuck bottles of Dom from a charity event at Martha's Vineyard and Chuck and Nate had managed to procure sundry party favors and they had all met at midnight at the small cove. Only Serena had invited along a new guy (whose name Blair couldn't recollect and she was even more certain Serena wouldn't be able to. They had never seen him since.) and Blair had been upset with her and so she had stormed away from the group and gone swimming.

In the heady haze of the moonlit night Blair had pretended to be a sea nymph. Always prone to cinematic notions, in her heightened state, she had felt like she was on the cusp of magic and discovery. Years later, Blair still kept the memories of that night close to her heart, for there, in the cool waters, she had chanced upon a revelation, for the first time in her life, she had felt free.

She had never been able to recall how the night had ended but thanks to countless retellings she had felt like she could play it out in her mind. Only in her dream, instead of Chuck pulling her out of the sea, struggling to swim back with her deadweight to the shore, he had been pushing her head back underwater. She could feel his phantom hands wrapped around her neck though she couldn't remember how the rest of the dream went.

Rubbing her eyes, she looked beside her where Nate was fast asleep. She swung her legs off the bed and tiptoed out of the room. She was still half asleep but her feet seemed to know where they were going. He always had the same room every time they visited during summers. She pushed the door open, only wishing she had knocked once she took in the scene that greeted her. Chuck was sitting on his bed, head tilted upwards, staring at the ceiling. A peroxide blonde bimbo kneeled in front of him, sucking him off. For a torturous second, Blair simply stood there, staring at them, before Chuck turned and looked directly into her eyes.

* * *

Blair Waldorf's lipgloss tasted sweet and sticky like candyfloss. Chuck Bass first discovered this fact years ago during a game of Seven Minutes in Heaven. Chuck had expected they'd go in the closet and he'd spend the seven minutes teasing Blair but she had surprised him by standing on her toes and pressing her lips against his even as her boyfriend stood on the other side of the door. It was by far the tamest activity Chuck had engaged in but he hadn't been able to get it out of his mind. It's just a game, she had said later.

An augury of the beginning of the end.

"Thought you'd be here," he said as a greeting, emerging from the hatch and onto the Widow's Walk. Blair was leaning against the railing, her back to him.

"I had a nightmare," she said casually, without turning around.

"If you are talking about walking in on me with my blonde nightcap, I am afraid that was all real."

She gave a little laugh at that, still not facing him. "Kinda wish it were that."

Chuck walked over and stood next to her, "What was it?"

"It was about that night I almost drowned. Do you remember it?"

"Yes."

"You saved me."

"Well, I do have a great radar for girls in swimsuits. Poor Nathaniel had headed off in the wrong direction."

"Right, anyway, as you remember I blacked out most of that night so I don't actually remember any of this."

Chuck remained silent, waiting for her to continue.

"In my dream, it was...twisted," Blair said, refraining from mentioning the exact change. She finally turned to look at Chuck and was taken aback by the concern in his eyes.

"You know, if being here brings back the memories.."

"No. It's not that. Technically, I don't think the brain forms memories during blackouts, so there'd be nothing to recall. My brain is just fabricating nonsensical scenarios and ruining my sleep."

"Well, you have always had the most nonsensical, not to mention, theatrical dreams."

"In this one you were killing me."

Chuck thought about what had actually happened that night so long ago. Given that Serena had fallen asleep and Blair had blacked out, it had fallen on Chuck and Nate to bear the burden of that memory. Chuck would have been okay with Blair believing her version of the dream if it meant that she'd stray further away from the reality. Suddenly, he felt protective of her and angry at the thought of her being troubled by that night, so many years later.

But Blair, having confessed the dream, felt released by it. Feeling lighter, she slipped her hand in Chuck's. "I guess I should apologize for my dream mind," she said, looking contrite.

Chuck smiled at her, pulling her closer. "Well, my one heroism, and you didn't even want history to remember it right."

The night was silent except for Blair's soft laughter and the singing cicadas. Chuck looked up at the moonless sky, inky-black and low, tiny pinpricks of light adorning it. And if he looked below, he could see the faint patterns of glowworms draping the trees. "Like fairy lights," Blair pronounced, following his gaze.

This night, Chuck thought, this was the one he wanted to remember.

"Oh, I guess I also owe you an apology for interrupting you back there," Blair said, with a sheepish smile.

"Interrupting? Is that what they are calling voyeurism these days?"

She shot him an indignant look which only served to motivate him further.

"Don't worry, I am not complaining. If anything, it helped me finish. She didn't have the most skilled-"

"Goodnight, Chuck," Blair said, pointedly.

It was only later, when they had stepped down and were making their way back to the rooms, that Chuck noticed Blair was in her night slip. It was a modest number by all accounts, and he had seen her in much less, but the view felt forbidden to Chuck and he averted his eyes.

* * *

The next morning everyone had gathered for breakfast at the long table on the lawn. By the time Chuck arrived, fashionably late, people were starting to splinter off. He stood at the edge, scoping out the crowd. There were a pair of supremely hot twins, who he vaguely recollected being introduced as Nate's cousins, but since Nate had always been indifferent to Chuck's conquests he was sure he'd similarly turn a blind eye at this. He was debating whether to make a move right away or wait till the wedding day which always seemed to put women in a festive and willing mood when he overheard Eleanor, having arrived just that morning along with the latest round of wedding guests, exchange a few words with her daughter before getting up to greet Anne Archibald.

Chuck took the vacated seat and helped himself to an éclair.

"Your mother can be a real bitch."

"It's too early in the morning for incivility," Blair said sharply. Though if she were being honest, he was quite right about her mother. Eleanor had only just gotten here, and her first words to Blair had been strict instructions to basically starve herself so she wouldn't _overwhelm_ the bridesmaid dress. She couldn't imagine how much worse her mother would get if it were Blair's own wedding. Still, she didn't want to discuss her weight issues with Chuck! It was already embarrassing enough that he had appeared to have overheard her mother. At least Nate had been far away..

Where was Nate anyway?

That morning he had rolled over in bed, never having noticed her missing in the night, and climbed on top of her. While still withholding her virginity from him, Blair usually put all her other feminine wiles on use to keep him satisfied. Today, however, when it had become obvious he was expecting her to give him head, she had balked, entirely opposed to the idea given that the scene she had witnessed between Chuck and his skank was still so clear in her mind.

Truthfully, Blair was worried Nate was getting tired of waiting. Even more truthfully, she was worried about her own waning interest in their relationship, which now that she was done with high school, already felt dated. She thought perhaps that if they could just last till her eighteenth birthday, when she would finally offer herself to him fully on the eve of her womanhood, she could restore her trust and love for him.

But sensing his disappointment from the morning, Blair was wondering if Nate would even remain faithful till the end of the summer. She also hadn't failed to notice that Serena seemed to be missing. And she wasn't with her own hipster boyfriend who was currently seated on Chuck's other side and looking at Blair with…pity?

Great, even Brooklyn had heard Eleanor.

Scowling intently at the croissants torturously displayed right in front of Blair's eyeline, she tried to remain calm as she politely sipped on her Darjeeling tea.

A lady never causes a scene.

A fat loser whose boyfriend is cheating on her and who is the object of pity of everyone around, however, is free to do as she pleases.

She stood up abruptly, and flounced away from her chair.

"Where are you going? You didn't even eat anything?" Chuck called out.

"Well, I am full on shame," she muttered before making her exit.

"Do you think she's alright?"

Chuck turned to look at the dark-haired guy who had spoken to him. "Who the hell are you?"

* * *

Blair had really only meant to enjoy one glass of rosé to soothe her nerves before their trip to Edgartown, but somehow that one glass had been followed by another, and now the bottle seemed suspiciously light.

"B, are you ready?" A sunny blonde head poked itself through her door and then emerged her sometimes best friend/the girl who was maybe sleeping with Blair's boyfriend.

"Oh, you look so cute!" Serena continued, looking at Blair's neat little sundress.

Blair barely managed not to roll her eyes at that compliment. _Cute._

She poured the precious last drops into her glass before throwing the bottle away.

"Let's go!" she chimed, in a false happy voice, perfectly mimicking Serena.

"Are you drunk?" Serena asked, cautiously.

Are you sleeping with my boyfriend?

"Yes. No. Maybe?" Blair muttered.

"I could use a drink, too," Serena said, falling in step besides Blair.

"Why, what have you been upto? I haven't seen you all day. Where were you?" Blair questioned, in the least accusing tone she could muster.

"Oh, nothing really. Just with Dan," Serena replied shiftily.

"Uh, huh," Blair nodded, not believing a word.

Meanwhile, downstairs, Chuck Bass was waiting for the others. He had never seen the island this crowded and bustling with life. Ahead of the wedding rehearsal tomorrow, the sheer number of relatives Nate seemed to possess was becoming apparent and Chuck couldn't help but feel a twinge of envy. There was a family tree hanging on one of the tall walls and he wondered what it might be like to be related to so many people by blood. His own riches paled in comparison: a father and an uncle. Surely, his father must have descended from others, but Bart Bass's origin story was privately guarded. And, well, Chuck had no interest in searching down his mother's side of the family when, knowing his luck, they probably blamed him for her death.

"Anything interesting, Bass?"

He turned to see Blair who had just arrived with Serena. Realising he had been caught staring at the wall for an inordinate amount of time, he quickly assumed an insouciant air.

"Just thinking of poor Nathaniel having to keep track of this large a family."

Even to his own ears, it sounded forced and unconvincing, and for a horrible second he was sure they were going to call him out on it.

But instead Blair just inclined her head. "What about you? Are we sure you don't have a couple of spawns crawling around all over the map?"

"Don't even joke about it," he stated in a mock serious voice.

"Come on, Nate and Dan are meeting us at the dock," Serena said.

As they all made their way to the dock, Blair leaned towards Chuck and whispered, "Thanks for last night."

"For killing you in your sleep?"

"For listening to me," she said, with a sincerity that the alcohol afforded her. "For talking to me."

"It was my pleasure, Waldorf," he said, and it dawned on him that he meant it.

* * *

 **A.N** \- So yeah, this is kind of a slow-build but I hope you guys stick it out with me. The plot really starts moving at the ~grand wedding~

Reviews are what keeps this lazy mermaid writing so _please_ review!


	3. Chapter 3

**A/N -** I think I already mentioned this at the beginning of the first chapter, but just to make it clear: This story is set in an Alternate Universe where Blair, Serena, Dan, Vanessa are about to start college, and Chuck, Nate, Carter, Georgina are 3 years elder to them. Hopefully it will make more sense when they all go back to Manhattan.

* * *

 **Chapter Three**

On the eve of the wedding, Blair found herself tiptoeing around the house with a determined expression. She should have been in bed right now, enjoying some well-needed beauty sleep, not sneaking around like a common thief but...well, this needed to be sorted once and for all.

"What are you doing?"

She jumped in fright as the voice emerged from the darkness.

"What are _you_ doing?" she half-whispered.

"I was doing the twins," he said, tilting his head towards the door he had just exited.

"Ew, how did you pull that off?" she asked, momentarily forgetting her quest. She had genuinely expected better from the Vanderbilt girls.

"It's the magic of weddings. Even incestuous threesomes can pass for romance. The desperation and neediness of girls really skyrockets," he said, before adding as an afterthought, "But I don't need to tell you that."

"Ugh. Goodnight."

Blair continued down her path only for Chuck to follow her.

"Are we stalking someone?" he wondered out loud.

" _We_ are not doing anything. _I_ have some business to take care of. Now, shoo!"

Chuck rolled his eyes. The fact that she was so keen on wanting him elsewhere only served to incite him further. And he could tell she was upto no good. But the direction she was headed seemed to indicate...

"Why are you being so sneaky just to visit Serena?" he asked puzzled.

Blair ignored him.

"You think she's sleeping with Nate?" he guessed.

"Well, he isn't in bed with me," Blair snapped.

"He is not cheating on you."

"How could you possibly know that?"

"He doesn't have the brainpower to hide an illicit relationship from both me and you. You are seriously overestimating his game here."

"For all I know he's in there fucking her and you're out here distracting me!" Blair responded, her voice rising sharply.

"Why are you acting so paranoid?" Chuck asked, taken aback by her hysteria. "Just because he cheated on you once? It means nothing."

"Except it does!" Blair said, turning around to face him. "It's not just about the cheating. He loved her," she confessed in a small voice.

Even in the dark Chuck could register the tears in her eyes.

"They dated after that, right, and it didn't work out so..," he trailed off when they became aware of faint voices coming from behind Serena's door.

Blair pushed Chuck towards the door and motioned for him to check if it was unlocked. She didn't think she could bear to witness Serena with Nate, or even Dan on the off chance she was with her own boyfriend.

She watched with bated breath as Chuck opened the door a little and drew out his phone, taking a quick photo.

"Come on," he said, pulling on her hand and moving away from Serena's room.

They remained silent till they entered his room.

"Well, I was right," he said, pushing the phone screen in front of her.

"Oh my god. I can't believe that I am saying this but this is actually worse than what I expected." She looked up to see Chuck wearing a smug expression on his face. "And fine, you may have been right," she continued, just wanting to be done with it.

" _May?_ "

"She could be sleeping with both of them!"

Chuck raised his eyebrow.

"Fine, I was wrong. You were right. Happy?" she finally conceded.

"Very," Chuck gloated, "But not as much as I am gonna be once we reveal this little piece of information and watch everything break out into chaos."

Blair thought about that admittedly attractive suggestion for a second before shaking her head resolutely.

"No way," she said, swiftly deleting the incriminating photo from Chuck's phone. "Humphrey may be a less than satisfactory choice for my best friend but at least he isn't getting married tomorrow."

* * *

On the day of the wedding, it seemed like everyone who's anyone was descending onto the island from their boats or jets. Members of the press, a horde of politicians and several minor royals were swarming around, which is why Chuck found it curious that William Vanderbilt found the time to summon him to his office.

The room was dimly lit, the morning light barred by the thick drapes, and Nate's grandfather was a mere shadow behind the large desk. Instead, Chuck found his eyes drawn to the maritime art which decorated the room: paintings depicting naval battles, models of 16th century Dutch warships.

"Do you know how to sail?" William asked, noticing Chuck's gaze. "Nathaniel spent quite a lot of time this summer sailing with his father. I taught him all the ropes myself when he was just a little kid."

"Yeah, he's mentioned that," Chuck said, taking a seat, and wondering why this topic of conversation was so urgent.

"I am sure you must have guessed why I called you here today."

Chuck, who had no idea what Nate's grandfather was talking about, was growing perplexed by the minute.

"I have been made aware of your late-night activities," he explained.

"Oh, right. The twins," Chuck said, nodding his head. He had completely forgotten William was their grandfather too.

"Not that," the old man replied, waving the matter away with his hands. "I am talking about Miss Waldorf."

"Blair?" Chuck voiced out loud, before another thought arose to his mind. Were there camera's everywhere? In which case…

"Does this mean you have also been kept upto date on Tripp's..what was it.. _late night activities_?"

William Vanderbilt took a pregnant pause before answering.

"I have spoken to Tripp and be rest assured after his marriage today, there will be no further troubles and he will do his part in keeping up our legacy. Now it's time for Nathaniel to step up."

"What has any of this got to do with me?" Chuck wondered out loud, already bored by the direction this conversation was taking.

"Nathaniel has always trusted you, even when your adolescent exploits-"

"What's your point?" Chuck snapped. He really had no interest in being berated by Nate's ancient grandfather. Not when he got enough of that from his own father.

"My point is that even if Nathaniel doesn't carry my last name, he was born to be a politician, and Blair Waldorf will make a great politician's wife-"

Chuck snorted incredulously. Between the two of his friends, Blair was the only one with an aptitude for machiavellianism, and Nate had never so much as shown even the slightest interest in politics.

"We just think they are very appropriate for each other and and I can only hope that you as Nathaniel's best friend would have his best interests at heart."

"Wait. Do you think I am sleeping with Blair?" Chuck asked, finally realizing what William was dancing around.

"Honestly, I don't care what you are doing with her as long as all of you are aware of your places," he said, standing up and opening the door for Chuck.

* * *

For all the secrets present behind locked doors, the ceremony went without a glitch. No one would have guessed that the groom had spent his last unmarried night with another woman as he looked at his new wife with adoring eyes. Chuck couldn't help but scoff at this farce of love and monogamy.

Even Blair, who had been a wreck last night, had looked pristine and cool as she walked down the aisle with Nate, the red-gold afternoon sun shining through stained glass and glinting on her dark hair.

Reception was a glittering affair and held on a bluff which overlooked the sea. Most people had vacated their seats in favor of the dance floor but Chuck sat at one of the round tables along with Carter Baizen and Uncle Jack. Chuck knew Bart had been invited but he had proclaimed himself much too busy for the event.

"God, do you remember when Tripp Vanderbilt used to be cool?" Carter said, shaking his head in disappointment as they watched the newlyweds clasping hands with an elderly relative.

Chuck thought about what he had witnessed yesterday and how Tripp wasn't nearly as strait-laced as he would like people to believe. He almost shared the information with Carter who had become good friends with him during their time together at Dartmouth but instead chose to keep it to himself. And though Blair had deleted the photo from his phone, it had automatically been backed up on a cloud. It would serve as a worthy ammunition in case he wanted to cause some trouble in the future, and after the delusional lecture William Vanderbilt had made him sit through this morning, Chuck was feeling rather unkind towards the family.

And unlike Nate, who Chuck trusted implicitly, there had always been a competitive streak present in his relationship with Carter, exacerbated by their mutual membership in The Empire Club, an undergraduate secret society at Dartmouth.

The society activities didn't really entail a lifestyle that was any different from the one he had followed back at home, if anything, at times, they seemed tamer- obligatory hazing, outrageous pranks on persons in authority, drug binges, sex shows on school grounds, solicitation, etc., but every little act was turned into a game of constant one-upmanship, and there was nothing quite like the thrill of winning, which Chuck always did. The Empire Club rewarded its members from their depravity, and while no one could quite beat him at that, Carter came close. Those games were the only part of college he would miss.

As if reading his mind, Carter volunteered, "How about we play a little empire game to celebrate the fact that neither of us is getting married?"

"What did you have in mind?" Chuck said, taking a sip of his scotch.

"I heard there was a Princess attending-"

"It's a Prince," Jack, who was listening to their conversation, corrected with a laugh. "Are you still interested?"

"Never mind, then," Carter muttered, rolling his eyes. "Let's go with a classic- The Deflowering."

"It might be easier to find you a Princess than a virgin," Chuck joked.

"Not so fast there, I think I have a suitable target in mind," Jack said.

"You are a fellow Emperor, so you picking the victim may be a good way to commemorate the beginning of the game," Carter acquiesced **.**

"Blair Waldorf," Jack declared, helpfully pointing them in the direction where she was revolving on the dance floor along with Nate.

Chuck gave a little laugh before realizing Jack wasn't joking. "Wait. Are you serious?"

"No, no, this is good. She is totally icy, and wasn't she the President of the Chastity Club at Constance? This could be a real challenge," Carter said.

"Have you both lost your minds? Have you forgotten who she is dating," Chuck bit out angrily.

"Like I said, a real challenge," Carter repeated.

"She's Nate's girlfriend," Chuck reiterated, wondering how he had ended up on the sensible side of the conversation.

"How does that matter? Nate wasn't in the Empire. He isn't one of us. Where exactly do your loyalties lie, Bass?" Carter asked, annoyed. He wasn't used to Chuck ever disagreeing to anything on moral grounds.

Chuck remained silent. He had only really joined the society to have something to do while at college, which in turn he had only attended after being forced by Bart and not because he possessed any academic interest. He had certainly never viewed it as a brotherhood they way the others seemed to, though he did appreciate the sense of belonging.

Carter took Chuck's silence as a hint to his answer.

"Okay. So you and Nate are "BFFs". But doesn't the fact that she is your best friend's girl serve to make it more interesting? Didn't you always say, the more twisted, the more you liked it?"

"Or maybe his hesitance doesn't have anything to do with dear Nate. Maybe there's some other reason you don't want to do this?" Jack prompted, with a cryptic smile.

"What other reason could there be?" Chuck asked, confused.

"Look, if you don't wanna do this, just say it. I saw Tarquin back there, and I am sure he'd be interested. So do you wanna back down? Are you in or are you out?" Carter said, impatiently.

Chuck would later wonder what inspired him to make up his mind about this stupid game- he must have known even then that nothing good could ever come of it, it may have been some primordial male instinct of never backing down from a challenge, or his proclivity for self-destruction, the copious amounts of alcohol he had consumed, or something else entirely, but either way he arrived at his damning answer.

"I'm in."

"Great, but we need to work out some fine points-" Carter started with enthusiasm.

"Later," Chuck said darkly, knowing Jack was still listening intently. He had always gotten along well with Jack, even looked up to him, but suddenly he felt like he didn't want to involve him any further in this. "Just one question," he added, lowering his voice so only Carter could hear, "aren't you worried I'll have an unfair advantage. I know you are acquaintances with her but she knows me well. We're friends."

"Actually, that's why I am so confident you'll lose. She knows you well," he replied, clapping Chuck on his back.

* * *

Blair could feel her eyes getting heavy. She had been up since dawn joining the bride in her preparations, and had barely gotten any sleep last night, consumed by guilt over wrongly suspecting Nate and also worried about Serena and Tripp.

Her best friend had skipped out on the wedding, pretending to be sick. Blair decided she would let her have today, but tomorrow she was getting to the bottom of this whole mess. Dan was present, awkwardly hovering around alone, since he didn't actually know anyone here except Serena. Knowing what she did, and having experienced the immeasurable pain of being cheated on, Blair almost felt sorry for him, though not as sorry as she felt for herself at having something in common with Lonely Boy.

If she had been in a more generous mood, she would have offered him a dance, or perhaps made small talk, but she was exhausted. Every bone in her body felt tired and the only reason she could stand upright was because Nate was holding her. Yesterday, after she had left Chuck's room and gone back to theirs, she had found him already in bed, fast asleep. She hadn't wanted to wake him up just to question him, so she had decided to forget about his disappearance. Her earlier paranoia that Nate and Serena were having an affair seemed like an ill-thought-out conclusion triggered by the insecurity that always came along with her mother.

But Nate still appeared distant, like he had something weighing down on his mind.

"Where were you last night?" she asked, trying to keep her voice casual.

As if startled by her question, he looked around and suddenly snapped alert.

"Hey, I just remembered something I was supposed to do. Is it cool if we meet back at the house?"

"Sure," Blair said, deflating as she realized he hadn't even registered her question.

He placed a quick kiss on her lips and walked away, leaving her stranded in the middle of the dance floor. For a moment, she just stood there, too tired to even move.

"Could I have this dance?" Chuck asked formally, walking up behind her. Before she could even respond, he took her hand.

His eyes were strangely cold and expressionless but his hands on her waist were warm and solid, and so she allowed him to guide her in a slow dance.

"Purple suits you," he remarked softly.

"Well, this is actually more of a lavender," Blair said, looking down her bridesmaid dress.

He cracked a smile at that.

"Okay then, lavender suits you."

She didn't say anything, just concentrated on the lights and music as he spun her around.

"Where did Nate go?" he asked her after a while.

She shrugged her shoulders, "I never know where he goes anymore. He's been acting so distant lately. Do you know anything that could be wrong?"

After all Chuck was his best friend. If Nate was upto something, surely he would know? Whether Chuck would share that information with Blair was another question altogether. With a sinking feeling, Blair realized she was once again being suspicious of Nate.

Chuck shook his head at her question.

"You know, I thought that I was over everything, but I guess I am not. I don't think I trust him anymore," she confessed.

Chuck thought about William telling him that Blair is Nate's future, he thought about Blair last night, tears clinging to her eyelashes, he thought about the game.

"You should break up with him," he said, looking her straight in the eyes.

* * *

 **A/N** \- And so the game begins!

(& this was in the summary so I hope no one hates me for it.)

Re the little mysteries that you may come across, it'll all be revealed in due time.

You know what fuels fic writing? Reviews! (Also, this way I can know what you guys like and what you don't like!)


	4. Chapter 4

A/N - I know I am updating this after like 2 years but I got into grad school at NYU and had no time for any fandom related leisure! I am in my last semester though now so I'm trying to enter in again. Hopefully, I'll soon have more free time. If there's still any interest in the fic let me know.

* * *

Blair had stormed off from the reception, angry at Chuck for being audacious enough to give her relationship advice, and even more angry that he was trying to act innocent about Nate's evasive behavior. Blair couldn't think of a single reason Chuck would want her to break up with Nate if he didn't suspect there was something unsavory going on.

She entered Serena's room without knocking, confident she won't find her with a guy this time. Serena was sitting in her bed, an old photo album in her lap.

"Hey, B, How was the wedding?" she asked nervously.

Blair took off her heels and climbed into bed with Serena, looking down at the photo Serena had been staring at. It was an old polaroid featuring Georgina and Serena atop a bar and Tripp looking up at them.

"I know," Blair said, too tired to keep up the pretense any longer.

"Know what?"

"Serena, drop the act. I heard you last night with Tripp."

"What were you doing outside my room? You are not even on this floor."

Blair halted, not wanting to disclose that she had been waiting to catch her red-handed with Nate. "Are you sure that's what you want to talk about after what I just revealed?" she asked instead.

Serena sighed. "Okay, fine, lay it on me."

"What were you thinking!?"

"I wasn't thinking."

"Which is exactly the problem! Anyone could have caught you! Can you imagine the scandal it would cause? And I don't mean high school infamy, but national level opprobrium!"

"I just got carried away. I love Dan but being back in this place with Tripp brought back so many memories, and I kinda fell for him."

"S, he's married. You shouldn't even be thinking such things, let alone saying them out loud."

"I know, but when we are together, it's so easy to forget that. And I don't think he loves Maureen."

Seeing that Blair's expression had remained unchanged, Serena sighed. "But I don't expect you to understand."

"What's that supposed to mean?"

"You are not exactly an impulsive person."

"I am plenty impulsive!" Blair exclaimed with annoyance.

"You do more than your fair share of ridiculous things but they are all planned out. You always follow your brain. I followed my heart and even though I can barely stand the guilt I'd do it again."

"I don't think _heart_ is the part of the anatomy you were following," Blair snapped. "If Tripp didn't want to be with Maureen, he could have easily done that. It's not like he was already a married man telling you he'll leave his wife for you. He had a choice and he didn't choose you."

"Have you met his family? He didn't have a choice. Romance is arranged when it comes to the Vanderbilts," Serena retorted.

"Excuse me?!"

"But..I mean, it's different with you and Nate, obviously," Serena said, trying to calm down her increasingly agitated best friend.

"You think Nate is only with me because of his family."

"No, I don't," Serena insisted, sincerely. "But you getting so worked up over this makes me believe that's what you think."

Blair simply sighed, collapsing on the bed. Maybe she shouldn't be giving Serena any advice when her own love life was hanging by a precarious thread.

"I don't wanna fight anymore," she said.

"So you won't tell anyone? Especially not Dan."

"I don't support you in this, but yes, I won't tell anyone. Though I am not so sure if Chuck will keep his mouth shut."

"You told Chuck," Serena screeched.

"No, I didn't! He was with me last night."

"What were you doing with Chuck Bass?"

"Hello, who exactly is supposed to be getting grilled here!"

* * *

Chuck had regretted uttering those words as soon as they escaped his mouth. He hadn't been aware he possessed a conscience but apparently back-stabbing his best friend brought it out on the surface in full force. But maybe Nate was actually cheating on Blair, he argued with himself, she certainly seemed to think so, in which case giving them a push towards a break-up was hardly a crime, more like a favor, if anything.

Let's not pretend your intentions are that pure, he thought, turning in bed again.

After Blair had walked off in anger, he had tried to forget the entire thing by drowning himself in scotch and a rendezvous with the leftover bridesmaids in the coatroom. But despite his best efforts, he couldn't take his mind of the game. He had spent a sleepless night, half wanting to go to Carter and tell him the deal was off.

Yes, he thought, it was safe to assume with the way Blair reacted that she wouldn't break things with his best friend, which meant she was off-limits, she would always be off-limits and he was just gonna have to swallow his pride and go tell Carter he was stepping back. First thing in the morning, he decided.

And with that thought and the couple of sleeping pills he had swallowed he found himself dozing off just as the sun started coming up in the eastern sky.

He was having a pleasant but highly inappropriate dream when soft curls brushed against his shoulder gently tickling him. In delicious languor he pulled her closer, placing his hands around her tiny waist. Her very real tiny waist, he realized suddenly, blinking up at her.

"What the fuck," he whispered. Had he actually managed to will her to his bed by simply wanting it enough?

"Language," she replied softly, before leaning down further to kiss him on his forehead.

"Okay, seriously what are you doing?" he said pushing her off him, suddenly wide awake.

"I was checking if you have fever," Blair exclaimed, the words sounding oddly maternal to Chuck.

"I am fine," he snapped at her, though the spot where she had placed the kiss seemed to be burning up.

"Are you sure?" she said, giving him a shrewd look, "You are-"

"Waldorf."

"Fine," she said getting up from his bed. "I was trying to wake you up for a while," she added in an annoyed voice.

"Not that I didn't enjoy waking up to this beautiful apparition, but was there a reason for this visit?" He tried to sound nonchalant but finding Blair in his bed, clad only in her little white swimsuit, seconds after featuring in his sex dreams was making him a little uncomfortable. He was also worried she might notice the hard evidence of just how much he enjoyed it.

He tried to discreetly adjust himself, in the process finally sitting up in his bed. As Chuck sat upright, the sheets slid down his body to reveal a naked torso.

"Are you not wearing anything under that?" Blair bit out, blushing slightly, but instead of covering her eyes in a girlish action like he had expected she would, she continued looking at him, her eyes following his happy trail.

"Well, I am always prepared incase some half-naked girl climbs into bed," he drawled, looking her up and down. He figured if she could check him out, he could do the same.

"Ugh," she muttered, finally tearing her eyes away from his bare chest and to his stupid smirk. She threw the nearest thing at him hoping it would wipe the pleased look off his face.

"Pillow fight, I am scared," he said sarcastically.

"Don't think I am above smothering you with it if you annoy me too much!" she said, placing her hands on her hips and giving him a stern look.

Chuck ducked his head and smiled, "I could never be unwise enough to underestimate you, Waldorf."

"So before you distracted me with your inane sleazy babble-"

"You mean before I distracted you with my devastatingly handsome good looks that you couldn't take your eyes off-"

"Inane sleazy babble," Blair repeated, ignoring him, "I came here to thank you."

"Really, what for?"

"What you said last night about Nate and how I should-"

"Blair, wait," Chuck said hurriedly, his good mood vanishing as he recollected the events of last night. He had to assuage her worries about Nate and then head up to Carter. "About what I said," he started, only to find himself interrupted.

"I broke up with Nate."

"You did what?"

"Yeah, it was a long time coming. I was talking to S last night and it just clicked."

"So why are you thanking me? It had nothing to do with what I said," he said, trying to distance himself from the break-up.

"Come on, you wouldn't have told me to end things with him if you didn't know something was up. And don't worry, I am not gonna badger you about his secrets, I get that you have to uphold the bro code or whatever it's called. And frankly, I guess the secrets don't concern me anymore."

He looked at Blair's relieved expression and opened his mouth to come up with something to reverse this chain of events, but unfortunately no words seemed to come out.

Blair turned away from him and walked to the window. "We are late! Get ready fast. I am going downstairs. Everyone's already there," she said peeking out.

"Late for what?"

"Did you forget The Edgartown Regatta is today!? Where's your head at Bass?" she snapped.

* * *

Thanks for reading and don't forget to leave a review.


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